Phosphorus oxychloride → 2-(1H-Imidazole-2-yl)-thiazole-4-carbonitrile

HRID 1594069Notes

Reaction equation

HRID 1594069 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[S:7][CH:8]=[C:9]([C:11]([NH2:13])=O)[N:10]=1.O=P(Cl)(Cl)Cl.C([O-])(O)=O.[Na+]>N1C=CC=CC=1>[NH:3]1[CH:4]=[CH:5][N:1]=[C:2]1[C:6]1[S:7][CH:8]=[C:9]([C:11]#[N:13])[N:10]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 136343466HCID 136343466, compound

Product 1

HCID 1357400962-(1H-Imidazole-2-yl)-thiazole-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-(1H-Imidazole-2-yl)-thiazole-4-carboxylic acid amide (120 mg) in 2 mL of anhydrous pyridine is added 0.25 mL of POCl3 dropwise at 0° C. The reaction mixture is stirred at the same temperature for 2 hours, poured into ice water, neutralized with solid NaHCO3, and extracted with 5% MeOH in CH2Cl2. The extract is washed with brine, dried and concentrated to a solid. 1H NMR (DMSO): δ 13.45 (br, 1H), 8.82 (s, 1H), 7.38 (s, 1H), 7.12 (s, 1H). LRMS calcd 176, found 177 (MH+).

Workup

  1. extractionextracted with 5% MeOH in CH2Cl2
  2. washThe extract is washed with brine
  3. customdried
  4. concentrationconcentrated to a solid

Sources & evidence

ORD record
ord-5b0089ca579d403698e1c5aa1e42abb3
Source dataset
uspto-grants-2007_11
Patent number
US07300945B2

Reaction notes

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